1. Field of the Invention
This invention relates to a novel process for preparing N-hydroxy organo imidate compounds. More particularly, this invention is directed to a process for preparing N-hydroxy organo imidate compounds by halogenating the corresponding oxime compound in an organic solvent which does not react with the halogenation agent under the reaction condition, and reacting the resulting 1-halo substituted oxime compound with the alkali metal or alkaline earth metal salt of an alcohol.
2. Prior Art
The classical method of preparing N-hydroxy organo imidate compounds involves reacting the corresponding iminoester hydrochloride compound and hydroxylamine hydrochloride. For example, J. Houben and E. Schmidt, Chem. Ber. 46, 3616 (1913), and Y. Tamura et al., J. Org. Chem. 38, 6 1239 (1973) describe the preparation of ethyl N-hydroxyacetimidate by reacting acetiminoethylester hydrochloride and hydroxylamine hydrochloride in accordance with the following reaction scheme: ##STR1## The reported yield was 66.3%.
A. Werner and H. Buss, Chem Ber. 27, 2193 (1894) has reported an attempted reaction of .alpha.-chlorobenzaldehyde oxime with sodium ethoxide, in which ethyl N-hydroxy benzimidate was identified along with diphenyl urea as reaction products.